Hydrochloric Acid → {3,5-Dichloro-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid

HRID 1515019Notes

Reaction equation

HRID 1515019 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9]([C:13]2[NH:17][C:16]3[CH:18]=[C:19]([C:22](=[O:34])[NH:23][C:24]4[CH:33]=[CH:32][C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]=4)[CH:20]=[CH:21][C:15]=3[N:14]=2)=[C:8]([Cl:35])[CH:7]=1.[OH-].[Na+].Cl>CO>[Cl:35][C:8]1[CH:7]=[C:6]([CH:11]=[C:10]([Cl:12])[C:9]=1[C:13]1[NH:17][C:16]2[CH:18]=[C:19]([C:22](=[O:34])[NH:23][C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[N:25]=3)[CH:20]=[CH:21][C:15]=2[N:14]=1)[O:5][CH2:4][C:3]([OH:36])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66965705{3,5-Dichloro-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid methyl ester

Product 1

HCID 66965254{3,5-Dichloro-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of {3,5-dichloro-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid methyl ester (100 mg, 0.19 mmol) in MeOH (3 mL) was added 1N NaOH (3 mL) and the solution was stirred at ambient temperature for 3 h. The solution was carefully acidified to pH 3-4 with 1N HCl and the suspension was filtered, washed with water, and the pale yellow solid was dried in vacuum oven to give the title compound. 1H NMR (Methanol-d4, 400 MHz): δ 11.14 (s, 1H), 8.46 (s, 1H), 8.43 (q, 2H), 8.02 (dd, 1H), 7.97 (d, 1H), 7.91 (d, 1H), 7.76 (m, 2H), 7.55 (m, 1H), 7.32 (s, 2H), 4.93 (s, 2H). MS (m/z) 507.3 (M+1); Retention time: 1.11 min (Method 10).

Workup

  1. filtrationthe suspension was filtered
  2. washwashed with water
  3. customthe pale yellow solid was dried in vacuum oven

Sources & evidence

ORD record
ord-3e527006622c42bb85563c8d3b3433bf
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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